Hydrazine hydrate (1:1) → 4-Methoxy-N-[2-nitro-4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]benzamide

HRID 2199055Notes

Reaction equation

HRID 2199055 reaction equation
O.[NH2:2][NH2:3].C[O:5][C:6](=O)[CH2:7][CH:8]([C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[C:13]([N+:28]([O-:30])=[O:29])[CH:12]=1)[CH3:9]>C(O)(=O)C>[CH3:9][CH:8]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:27])[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:13]([N+:28]([O-:30])=[O:29])[CH:12]=2)=[N:3][NH:2][C:6](=[O:5])[CH2:7]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13850879Methyl 4-[4-(4-methoxybenzamido)-3-nitrophenyl]-3-methyl-4-oxobutanoate

Product 1

HCID 138508804-Methoxy-N-[2-nitro-4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

20 ml of 80% hydrazine hydrate were added dropwise to 150 ml of glacial acetic acid while stirring and ice cooling. After cooling, 10.7 gm of 3-[3-nitro-4-(4-methoxybenzoylamino)-benzoyl]-butyric acid methyl ester were added and the mixture was refluxed for 40 minutes. After cooling, 250 ml of ice water were added, and the precipitate formed was suction filtered and washed with ice water.

Workup

  1. temperatureAfter cooling
  2. temperaturethe mixture was refluxed for 40 minutes
  3. temperatureAfter cooling
  4. customthe precipitate formed
  5. filtrationfiltered
  6. washwashed with ice water

Sources & evidence

ORD record
ord-b16d983df6a2450f953bec25d7319a15
Source dataset
uspto-grants-1982_11
Patent number
US04361563

Reaction notes

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